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Holiday rentals in Charleston

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Charleston

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Home in Mattoon
4.95 out of 5 average rating, 262 reviews

Brickway Retreat

Newly Remodeled 2 Bed, 1.5 Bath home in quiet neighborhood. This modernized house features a large fully furnished kitchen that is open to the dining area. The large living room with 10 ft ceilings has a pull-out sofa. Big screen TVs equipped with Roku streaming service in the master bedroom and living room. Wi Fi throughout the house is included. Enjoy your mornings on the cozy front porch featuring cedar pillars and stamped concrete and enjoy your evenings on the back patio around the fire pit

Top guest favourite
Bungalow in Greenup
4.99 out of 5 average rating, 166 reviews

Craftsman Bungalow Guest House

Welcome to the Craftsman Bungalow Guest House. This special place is close to everything, making it easy to plan your visit. It is a 1930's Sears Craftsman home located near downtown Greenup, about 1 mile from Rt 70. Greenup, known as the Village of the Porches between Interstate 70, IL RT 40 and IL RT 130, with over 1500 residents. Our Main Street (Cumberland St/Il Rt 121) is also part of the National Road, attractive old architecture, beautiful overhanging porches leading to our Covered Bridge

Top guest favourite
The cottage exterior is illuminated at night, featuring a welcoming porch with wooden columns. Two rocking chairs and a small table are positioned on the porch, surrounded by seasonal decorations. The pathway is lined with smooth stones, leading to the entrance.
Cottage in Sullivan
5 out of 5 average rating, 262 reviews

3-Acre Country Escape | Wildlife | Total Serenity

A freshly updated cottage, nestled in the country of Sullivan, just minutes from boating, camping, golf, theatre style shows, Amish country, and more. If you are looking for peaceful nights, this place is for you! Surrounded by mature trees and nature, where many days you will catch deer roaming the yard. Plenty of yard space for games, a fire table to converse around, and chairs on the porch to sit back, relax, and take in the tranquil sounds that surround you here at Lakewood Cottage #1.

Top guest favourite
A renovated red caboose, TP&W 527, is positioned on railroad tracks surrounded by grass. The structure features white wheels and an elevated cupola, with windows and a yellow emblem. Green trees provide a natural backdrop, and a cobblestone pathway leads to the entrance.
Train in Oreana
4.99 out of 5 average rating, 149 reviews

The Caboose on Mayberry

Welcome to our mid 1900s caboose TP&W 527 and step back in time. Unwind and relax as you settle into your retreat. Enjoy the view from the cupalo as you browse through one of the books on board, or sit at your dinette and enjoy a board game. Sit out back in one of the adirondack chairs around your own private fire pit and enjoy s'mores, or just a peaceful evening. The caboose has been completely renovated and many modern convienences added. You'll love this unique and romantic escape!

Top guest favourite
Place to stay in Greenup
5 out of 5 average rating, 254 reviews

The Candy Kitchen

Take a step back in time as you enter this authentic 1930's Soda Fountain located in downtown Greenup Village of the Porches situated on the Historic National Road. The Loomis Family immigrated from Greece and operated the Soda Fountain and Confectionary until the 1960's. It has since been transformed into a spacious and comfortable living area with the original Soda Fountain still intact, beautiful tin ceiling, and also includes a large kitchen, a separate shower room & powder room.

Top guest favourite
Home in Teutopolis
4.96 out of 5 average rating, 248 reviews

Wooden Shoe Factory, Historic, w/ Bar & Breakfast

Historic 1880 Wooden Shoe Factory by Wooden Shoe Maker Gerhard Deymann. A great getaway Tiny House from the past with a Bar & Books. Please take some & leave some :-) Fully furnished. Tons of charm. It has a loft, luggage lift, exposed brick/beams, fireplace, bikes, antiques, front sitting area, swing, grill, back patio, yard, private parking, appliances, vaulted ceilings. 6 minutes to I57, I70, Effingham, & dozens of restaurants. 1 block to 7 Teutopolis Bars, & diners.

Top guest favourite
A large tree with a sign reading '9330 The Cabin' is visible in the foreground. A gravel driveway leads to the cabin, framed by lush, green trees that create a serene natural environment.
Cabin in Ashmore
4.89 out of 5 average rating, 297 reviews

Sweet Dreams Cabin. Peaceful & Relaxing

Get some quality family time at this newly remodeled cabin near the beautiful Embarrass river. You are surrounded by beautiful woods and a small creek. Lush wildlife is all around you so you can be one with nature. The cabin has all the luxury's to allow for a long term stay as well. Beautiful Lake Charleston is not far away. The large circle drive offers plenty of parking for your boat and guest. The large deck on the rear gives a beautiful view to be enjoyed by all.

Top guest favourite
The entrance features a white door framed by blue and white siding. A welcome sign is prominently displayed beside the door, complemented by a potted plant at the base of the steps. Sunlight brightens the area, highlighting the welcoming ambiance.
Flat in Arthur
4.98 out of 5 average rating, 308 reviews

The Hideaway - Charming apartment in Arthur IL

Enjoy exploring Illinois' largest Amish settlement while relaxing in this one-bedroom apartment one block from downtown Arthur, a village of 2200. Country charm abounds in this gem which sleeps three (full bed plus fold-out love seat). There is a private entrance, access to laundry facilities, and private parking off the street. We are 9 miles west of I-57 on Route 133 (take exit 203 at Arcola) and 40 miles from Champaign.

Top guest favourite
The exterior of Mill Creek Farmhouse features a charming porch with intricately designed wooden trim. A welcoming sign is positioned at the base, complemented by decorative elements such as potted flowers. The house is surrounded by trees, adding a natural backdrop to the scene.
Cottage in Marshall
4.94 out of 5 average rating, 134 reviews

Mill Creek Farmhouse

Soon the boats will be cruising across Mill Creek Lake in search of catch of the day or enjoying some water-sports. While you are in the area make plans to stay at the Mill Creek Farmhouse. Enjoy an outdoor fire pit while having the entire house to yourself. In 15 minutes from the driveway you can have your boat launched and then come back to plenty of room for your family to enjoy their evening. Hope to see you soon!

Top guest favourite
A cozy seating area features a brown leather armchair positioned near a large sliding door. Natural light streams in, illuminating wooden walls and floors. The door opens onto a deck overlooking the tranquil lake, enhancing the indoor-outdoor connection.
Cabin in Mattoon
4.95 out of 5 average rating, 185 reviews

Cottage on Lake Paradise,

Welcome to Paradise Cottage nestled on Lake Paradise! Cozy and warm with wood finishes throughout. Includes three-tiered deck/patio, with the lowest level sitting over the water. Perfect for fishing (this lake hosts an annual fishing tournament), canoeing/kayaking, or just relaxing. Great for bird watching, with great blue herons, egrets, ducks, bald eagles, plovers, cormorants, woodpeckers and other species seen daily.

Top guest favourite
A spacious outdoor area features a covered porch with seating options, including a swing and chairs. Lush green grass expanses surround the property, complemented by trees in the background. The building's steel exterior reflects the natural light under a partly cloudy sky.
Loft in Charleston
4.99 out of 5 average rating, 108 reviews

On Harmony Lane...Cozy Loft apt in the Country

Our loft is the perfect place to rejuvenate in a country setting. From cozy bed sheets, TVs, and Wi Fi inside, to a firepit, grill, and hammock chairs outdoors, we make your stay comfortable. We are minutes from Eastern Illinois University. So enjoy...go antiquing, visit a winery, or delve into Lincoln's history. Visit a nearby Amish town. Go kayaking, fishing or enjoy a hiking on a nearby trail or one of ours.

Guest favourite
The exterior of a single-story house is shown, featuring a beige façade and a sloped roof. Front windows allow natural light, while a small porch is visible. A well-maintained yard includes green grass and neatly placed flower borders, offering a welcoming appearance.
Home in Arthur
4.92 out of 5 average rating, 292 reviews

Sojourners' Abode

Our family has enjoyed good experiences staying at AirBnb houses when traveling, so we decided to provide a place for others coming to our community. Arthur often has lots of activity, but this home away from home will be a peaceful spot for you to unwind. Just half a dozen blocks from downtown, but on a quiet dead-end street. Now with new faster wi-fi connection. Round up a few friends & come enjoy your stay.

Popular amenities for Charleston holiday rentals

When is the best time to visit Charleston?

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Avg. price€113€94€106€117€68€43€44€49€77€127€130€77
Avg. temp-4°C-1°C5°C11°C17°C22°C23°C22°C18°C12°C5°C-1°C

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Charleston?

    Charleston has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Charleston?

    Experience the best of Charleston with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Charleston?

    Yes! Work meets play with ease at over 10 vacation rentals in Charleston featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Charleston have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Charleston. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Charleston have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Charleston. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Charleston have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Charleston. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Charleston have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Charleston. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Charleston?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with free parking, over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Charleston

  • Total holiday rentals

    Explore 20 holiday rentals in Charleston

  • Nightly prices starting at

    Charleston holiday rentals start at €17 per night before taxes and fees

  • Verified guest reviews

    Over 400 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Charleston holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Charleston rentals

  • 4.9 Average rating

    Charleston stays are highly rated by guests – averaging 4.9 out of 5!

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